nitroalkenes

Now, researchers led by Mikiko Sodeoka from the RIKEN Advanced Science Institute in Wako have developed an innovative way to connect organic molecules known as nitroalkenes and α-ketoesters together with precisely controlled geometries1.

R&D Mag - News 2010

In looking at the molecular structure of the PBN nitrone spin traps, I recognized a familiar structure, one that is seen in the Michael acceptor pharmacophores in cinnamic aldehyde, the curcuminoids found in turmeric, and the nitroalkenes described earlier in this chapter.

Forever Young M.D. Nicholas Perricone 2010

These mild electrophiles are the active constituents found in watercress and the spices cinnamon and turmeric, and unique substances known as spin traps and nitroalkenes.

Forever Young M.D. Nicholas Perricone 2010

Like the nitroalkenes, it is classified as a Michael acceptor.

Forever Young M.D. Nicholas Perricone 2010

As in the case of nitroalkenes and the spices and spin traps I will discuss later in this chapter, this is a mild effect that is not detrimental to the cell structure; however, it is strong enough to trick the protective transcription factor NRF2 into thinking that there is severe oxidative stress present.

Forever Young M.D. Nicholas Perricone 2010

As we know, nitroalkenes are slightly electrophilic or mild oxidizing agents.

Forever Young M.D. Nicholas Perricone 2010

In addition to activating the good guys, mild electrophiles like the nitroalkenes, the curcuminoids found in turmeric, active constituents of watercress and cinnamon and the spin traps, deactivate the bad guys, just as we observed with the catechins found in blueberries, cocoa, and tea.

Forever Young M.D. Nicholas Perricone 2010

As we have learned, the nitroalkenes—nitrolinoleic acid, for example—strongly bind to and activate the PPARs, resulting in even greater weight loss, partitioning of energy, and uncoupling of oxidative phosphorylation.

Forever Young M.D. Nicholas Perricone 2010

As for cinnamic aldehyde, the curcuminoids, and the nitroalkenes, I believe the anticancer activity and other therapeutic benefits of a nitrone spin trap results from the fact that it is a mild electrophile and a Michael acceptor pharmacophore.

Forever Young M.D. Nicholas Perricone 2010

After several trials, the researchers determined that nickel catalysts, which share similar properties to palladium materials, allowed the α-ketoesters to add to nitroalkenes with high yields and purity; over 90% of the final product corresponded to a specific stereoisomer, a molecule with a hard-to-achieve, geometrically distinct structure.

R&D Mag - News 2010